Multiple redirects is a really bad idea and should be corrected whenever possible. The consideration I ask clients to understand is how multiple redirects amplify the loss of link juice. The numbers I will use in the below example are simply how I explain it when asked, and I don't have any solid math to back it up. As we all know, the exact process is kept secret.
Redirect #1 = lose 10% link juice
Redirect #2 = 1st link loses 10%, 2nd link loses 10%x2=20%, total 30% loss
Redirect #3 = 1st link loses 10%, 2nd link loses 20%, 3rd link loses 30% = 60% loss
Redirect #4 = 100% loss.
Again the numbers are likely not that dramatic, but it helps get site owners out of the mindset of "well, a 301 loses just a drop of link juice so 3 or 4 redirects doesn't lose much". We know the trust factors for a site rapidly diminish in an amplified manner a few links away from the source. We know PR on a site evaporates almost completely 4 links into a site. Even top PR sites like DMOZ and Yahoo directory have pages not indexed because there is not enough PR passed through their links to pages on their site which are deep. It is logical to think this same concept applies to redirects. It is another form of following links.